Name: Retired Boston Detective | This Past Weekend w/ Theo Von #616
Uploaded: 2025-10-09T15:11:28.000Z
Description: Watch the stand-up comedy video 'Retired Boston Detective | This Past Weekend w/ Theo Von #616' from Theo Von on Comedy Buff. Published 2025-10-09. Transcript available.

Watch the stand-up comedy video 'Retired Boston Detective | This Past Weekend w/ Theo Von #616' from Theo Von on Comedy Buff. Published 2025-10-09. Transcript available.

Retired Boston Detective | This Past Weekend w/ Theo Von #616

Before we begin, I'd like to say that some of the conversation from today is
kind of graphic in
nature. We're talking about police work and detective work and some of its intents.
If those
types of conversations are not for you, then please make that choice for
yourself. Thank you.
Today's guest is a retired Boston police officer and detective. She had over 20
years on the force
before she joined the human trafficking unit and fought criminals in that world.
We learned a lot
about what it's really like out there, and I want to thank her for her service.
Today's guest is Miss
Cara Connelly.
Yeah, I've been losing some hair because of stress.
Yeah, it happens. Sucks. You just go in the sink and you got handfuls.
Yeah, you just wake up and it looks like you look back and you're like, oh, who
was-
On your pillow, yeah. It's gross.
Your pillow's got sideburns on it or something. You know, your pillow's using a
curling eye.
It's a mess, yeah. Same.
It's way too much. You've dealt with it?
Yeah, in the past, yeah.
Yeah? And was it stress from work?
Yeah, and other things, but the Minoxidil definitely helps because I called my
doctor and they're like,
oh, she can't see you for nine months. And I was like, well, my fucking hair's
falling out.
And they're like, well, you can see the nurse practitioner in two months. I was
like, no.
So I went to one of those online things and they sent me Minoxidil in like
three months.
I had little bald baby hairs sprouting out and it came back. So it does help.
Yeah. Yeah, yeah. That's what I'm realizing. I just got to, yeah, just taking
some time just to enjoy,
do things just that I enjoy. That's what I'm, that's like my focus right now is
just to do things
that I enjoy. Um, because I'll, I'll let added stress stay on me as well. You
know?
Yeah, of course. That's what I'll do.
And it builds up.
Yeah. And not realizing that everything's going to be okay. You know?
That's my, my boyfriend's here with us. And when I was nervous about today and
he's like,
it's all going to be okay.
Yeah. It really is.
Like those latitudes.
Yeah. Everything's going to be okay. Um, Kara Connolly, thank you so much for
joining us.
You are a retired, uh, police officer and detective from Boston.
That's correct.
And, uh, you were on the forces for 30, 31 years, 31 years.
Yeah.
And you started out in Dorchester, I think.
Yeah. When I graduated the police academy, um, they send you to a couple of
different places to tell you,
you're on probation or whatever. And I went to a part of a city called Dorchester.
Wait, probation. They send.
So when you, you join the police department and you go through the police
academy.
Okay.
And then when you get out now they do it for a year, but when I did graduated,
it was six months
and they have you, um, you basically it's probationary period to see if you're,
you know,
good enough, behave enough or do the right thing, um, for like six months. So
they send you to a
couple of different places, like one busy district, one quiet district.
So they start you like a probationary period somewhere.
Yes. And you might stay there or they might move you, but that's how you're on
probation for six
months. And then you're, you know, a full-time police officer after that.
Okay. And what were those first years on the force? Like, um, like in South
Boston, was it?
Yeah. So I was actually born in South Boston. So I was in Dorchester and I was
in South Boston.
South Boston at the time was a quieter district. Dorchester was very, very busy
in the nineties
was like in Boston was a ton of shootings and gang stuff going on. Um, so
comparatively speaking,
South Boston was, was a quieter place to end up for several years.
And what were the demographics of that area? Like where you were servicing?
Uh, kind of everywhere. Um, Dorchester is a different, um, a different
demographic in South
Boston, um, population wise. Now South Boston's very hip and like, it's all
young kids. But with
the time I was, it was like all just kind of families, um, pretty quiet place
at the time
compared to other districts where like, you know, shooting every couple of days.
So.
And is it mostly white, black, Latino, Asian?
Dorchester at the time when I was first, there was, um, a lot of black, some
white, some Asian,
um, and South Boston at the time was mostly white, but, but some black and
Latinos.
Got it. And who are the people they call Southies? Cause you hear that a lot.
Southies is not a thing. Um, you could say you're from Southie, but it's not,
it's not,
it's not, it's not pluralized. There's no S on the end of it. But, um, so I'm
from Southie,
but I never said that growing up. We always said South Boston, but most people
said I'm from Southie.
Okay.
It's just a nickname for the part of town.
Right. But so, so you're not like, do, but do other people call you Southies?
Those are Southies?
No. People from like out of the city who hear about it became popular because
it was in
Goodwill Hunting was in South Boston. So that's kind of what put it on the map.
So when people
started moving there and didn't know any better, that's how they would say it.
But people who grew
up there back in seventies, eighties or whatever, didn't say it like that, that
pub that they,
you know, they filmed in became like a big thing, L street tavern. And, and, uh,
that was like
around the corner from where I grew up.
And, and were the people there distrustful of police at the time? What was the
relationship
like between no people in Southie, like, like the cops have compared to other
parts of the city.
Yeah. I think in my experience, I mean, it was a quiet place when I worked
there. Most of the stuff
that kind of good stuff that happened or whatever crazy or calls I've been on
happened when I was a
detective patrolman was pretty quiet. Do you remember one of your first like
big, like calls as a
patrolman that was like, Oh, this is real. Like, do you remember that? Like a
first moment where you're
like, this is pretty real. Well, a lot of the calls, that's funny. A lot of the
calls when, um,
it comes in like, you know, person with the gun call. Like I still remember my
first person with
the gun call. I was shit in my pants. Cause I was like, Oh my God, you know, it
turned out to be
bullshit. It wasn't even real. So a lot of the calls are like that. You don't
know they're fake
until you get there. So you're like your adrenaline dump in the car and you're
like, Oh my God, this
is real. And I remember being like, what am I going to do? No, that was a big
nothing burger.
Were you putting lipstick on or what do you even do? No, there was no lipstick
when I was a
patrolman. No. Yeah. Like, would you like powder up your face a little bit or
something?
No, no one powdered their face on the way to a call.
That wasn't it.
Yeah. That's just in Charlie's angels. Huh? Yeah. What was it like being an
officer in the
nineties in that time period? Like, was that way different than you think it is
now?
Yes, I think so. I mean, obviously the, the gang, the, the rate of shootings in
Boston was
much higher than, um, I forget what our highest homicide rate was in the early
nineties. It might've
been like 150, 160 people. Now Boston has like 35 a year. So it was a big
difference. Uh, it's, it's become
much safer whether everyone, the gangs kind of aged out and they all went to
jail or, you know, got shot
or moved on in life, whatever happened, it became, um, much safer. I'd say
there's no money in being in a gang
either. I think a lot of people were like, Oh, this is a shitty business. You
know? Um, this says 1990,
the homicide peak, Boston's homicide count hit an all time high of 152 cases
with much of the violence
concentrated among youth and in, and involving firearms. Um, the spike was
driven by gang violence,
crack cocaine epidemic, and easy access to handguns. Yeah. So the nineties are
a little different than
now for sure. Compared to then, how do you feel like police work is different
between now and then?
Do you have any thoughts on that? I don't know. I mean, the whole like
community policing aspect
aspect started when I was new. So that that's kind of still progressed along. I
think they're going
any community policing. Well, that's what they call it. At the time they had
walking beats. So
when I got on, um, you wouldn't be in a cruiser, like you'd walk the
neighborhood kind of like they
do in, in New York city. They have people walking around. There's not a lot of
cruisers. And so they,
they would put people in certain parts of the city. Like when I got on, for
example, and I worked in
Dorchester, I think there were like seven or eight walking beats up and down,
like kind of the main street
in the town. And now, excuse me, there's only a couple and they just put those
on again. So they're
kind of trying to get back to that. Um, so that was very different. Like people
who did the walking
beats full time, like knew everyone in the neighborhood. That was the whole
purpose is
to get people into the neighborhood. So people feel comfortable speaking to the
police, except
the neighborhoods where they put the walking beats were usually the worst
neighborhoods and people
didn't give a shit. They didn't want to talk to us. So it didn't matter anyway.
No, not the parts of
the city where they had them now. It's, it's different. Um, they don't have as
many walking beats at
all. They, they push a lot of the social media stuff. Like the dance, the
dancing cops is the
worst. It's so cringy. And they, the department, all the police departments do
that. They put it
out to try to be like, look, we're excessive. Oh, see, it's so, so embarrassing.
I haven't even seen
this. It's just, it's so goddamn cringy. Are these real cops? That's usually
the, I don't know about
them. Yeah. It says they are. Oh my God. Well, at least, at least they can
dance. Like when I,
when our department puts it out, it's like, she's like, right. Cop's like, look,
we're playing
basketball with the kids. And you know what? Let's all do these, especially
during COVID. It's just,
it's so cringy. They just put it on the other day from female, uh, woman,
police law enforcement
day. And they had like women dancing and some of my girlfriends and I sent it
back and forth. Like,
this is so. Who wants to see? Dude, the last thing I want is my cop dancing
over there. Is that
what you're looking for when you call for help? Someone to show up at sat
dancing? Like you want
someone who's gonna give you a hand. Yeah. It's just, I know they're trying to
soften their image.
They don't want to look like paramilitary anymore. They want to look friendly
and not scary and
whatever, whether it works or not long-term, I don't know. Yeah. You get
promoted to detective in 2005?
2007. 2007. Yeah. Okay. And what is, what, what does it mean to, to become a
detective? What does that
mean exactly? So to become a detective back then you had to take an exam. So it's
like a six month
to year long process. You have to study for several months and there's like six
or seven textbooks you
have to read. So you take the exam and then they do kind of like an oral
interview depending on how
you score on the test. And then they kind of combine your years of training and
experience,
your test score and your interview to say, okay, these people have been high
enough score to get
made detective. So, and then you do like a month's worth of training back at
the police academy
because being a detective versus a patrolman, it's very, very different. First
of all, you don't wear a
uniform, which is my favorite part, but it's just completely different job.
Like you're now
responsible. Cop gets a call, they go to the call, they write a report, and
that's the end of it until
they have to go to court. If the report that the cop writes about, it gets
assigned to a detective and
now you own that. Like, so you have to follow through, you have to follow up
and go to court or take out
criminal charges or whatever. So it'